Silicon Effect on the Enantioselective Transcyanation of Acetyltrimethylsilane Examined by Different Oxynitrilases  

作　　者：Sen Lin LIU Min Hua ZONG Shun Rong HUANG 

机构地区：[1]College of Life Science, Shenzhen University, Shenzhen 518060 [2]Biotechnology Department, South China University of Technology, Guangzhou 510640 [3]College of Life Science, Northeast Normal University, Changchun 130024

出　　处：《Chinese Chemical Letters》2005年第10期1317-1320,共4页中国化学快报（英文版）

基　　金：This research was supported by the National Natural Science Foundation of China(No.20376026);the Science Foundation of Shenzhen City(No.200325).

摘　　要：The synthesis of optically active （R）- and （S）-2-trimethylsilyl-2-hydroxyl propionitrile by enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin was successfully carded out using defatted plum, loquat , peach, almond or apple seed meals as （R）-oxynitrilase source and using Manihot esculenta leaves as （S）-oxynitrilase source in a biphasic system with good conversion and high enantiomeric excess. Comparative study demonstrated that silicon atom in substrate showed great effect on the reaction and due to the unique characteristics of silicon atom, both the substrate conversion and the product e.e. of the transcyanation of acetyltrimethylsilane were much higher than those of its carbon counterpart 3,3-dimethyl-2-butanone for all examined oxynitrilases.The synthesis of optically active （R）- and （S）-2-trimethylsilyl-2-hydroxyl propionitrile by enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin was successfully carded out using defatted plum, loquat , peach, almond or apple seed meals as （R）-oxynitrilase source and using Manihot esculenta leaves as （S）-oxynitrilase source in a biphasic system with good conversion and high enantiomeric excess. Comparative study demonstrated that silicon atom in substrate showed great effect on the reaction and due to the unique characteristics of silicon atom, both the substrate conversion and the product e.e. of the transcyanation of acetyltrimethylsilane were much higher than those of its carbon counterpart 3,3-dimethyl-2-butanone for all examined oxynitrilases.

关 键 词：Enantioselective transcyanation CYANOHYDRIN OXYNITRILASE acetyltrimethylsilane. 

分 类 号：O623.42[理学—有机化学]